Punicalagin
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MedKoo CAT#: 112149

CAS#: 65995-63-3

Description: Punicalagin is a major ellagitannin found in pomegranates that is reported to produce antioxidant, anti-inflammatory, and anticancer effects.

Chemical Structure

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Punicalagin
CAS# 65995-63-3
Instruction

Theoretical Analysis

MedKoo Cat#: 112149
Name: Punicalagin
CAS#: 65995-63-3
Chemical Formula: C48H28O30
Exact Mass: 1,084.07
Molecular Weight: 1,084.720
Elemental Analysis: C, 53.15; H, 2.60; O, 44.25

Price and Availability

Size Price Availability Quantity
25mg USD 300 2 Weeks
50mg USD 550 2 Weeks
100mg USD 950 2 Weeks
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Synonym: Punicalagin

IUPAC/Chemical Name: 1,2,3,12,13,14-hexahydroxy-5,10-dioxo-8-(14,15,16,22,23,27,28,34,35,36,7-undecahydroxy-25,210,4,10-tetraoxo-25,210-dihydro-5,9-dioxa-2(1,6)-chromeno[5,4,3-cde]chromena-1,3(1,2)-dibenzenacyclodecaphane-6-yl)-5,7,8,10-tetrahydrodibenzo[f,h][1,4]dioxecine-7-carbaldehyde

InChi Key: SKNLUADAGHCXKF-UHFFFAOYSA-N

InChi Code: InChI=1S/C48H28O30/c49-5-16-40(76-46(70)9-3-13(52)28(56)32(60)18(9)17-8(44(68)74-16)2-12(51)27(55)31(17)59)39-15(54)6-73-43(67)7-1-11(50)29(57)33(61)19(7)21-25-23-24-26(48(72)78-41(23)37(65)35(21)63)22(36(64)38(66)42(24)77-47(25)71)20-10(45(69)75-39)4-14(53)30(58)34(20)62/h1-5,15-16,39-40,50-66H,6H2

SMILES Code: O=C1OC(C(O)=C(C(C2=C(C(O)=C(C=C2C(OCC(C(O3)C4C(OC(C5=CC(O)=C(C(O)=C5C6=C(C=C(C(O)=C6O)O)C(O4)=O)O)=O)C=O)O)=O)O)O)=C78)O)=C7C9=C1C(C%10=C(C(O)=C(C=C%10C3=O)O)O)=C(O)C(O)=C9OC8=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 25.0 23.05
DMSO 10.0 9.22
Ethanol 15.0 13.83
PBS (pH: 7.2) 5.0 4.61

Preparing Stock Solutions

The following data is based on the product molecular weight 1,084.72 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Berdowska I, Matusiewicz M, Fecka I. Punicalagin in Cancer Prevention-Via Signaling Pathways Targeting. Nutrients. 2021 Aug 9;13(8):2733. doi: 10.3390/nu13082733. PMID: 34444893; PMCID: PMC8400644.


2: Fang L, Wang H, Zhang J, Fang X. Punicalagin induces ROS-mediated apoptotic cell death through inhibiting STAT3 translocation in lung cancer A549 cells. J Biochem Mol Toxicol. 2021 Jun;35(6):1-10. doi: 10.1002/jbt.22771. Epub 2021 Mar 15. PMID: 33720461.


3: Zhang L, Chinnathambi A, Alharbi SA, Veeraraghavan VP, Mohan SK, Zhang G. Punicalagin promotes the apoptosis in human cervical cancer (ME-180) cells through mitochondrial pathway and by inhibiting the NF-kB signaling pathway. Saudi J Biol Sci. 2020 Apr;27(4):1100-1106. doi: 10.1016/j.sjbs.2020.02.015. Epub 2020 Mar 4. PMID: 32256171; PMCID: PMC7105651.


4: Ganesan T, Sinniah A, Chik Z, Alshawsh MA. Punicalagin Regulates Apoptosis- Autophagy Switch via Modulation of Annexin A1 in Colorectal Cancer. Nutrients. 2020 Aug 13;12(8):2430. doi: 10.3390/nu12082430. PMID: 32823596; PMCID: PMC7468705.


5: Xu J, Cao K, Liu X, Zhao L, Feng Z, Liu J. Punicalagin Regulates Signaling Pathways in Inflammation-Associated Chronic Diseases. Antioxidants (Basel). 2021 Dec 24;11(1):29. doi: 10.3390/antiox11010029. PMID: 35052533; PMCID: PMC8773334.


6: Tang J, Li B, Hong S, Liu C, Min J, Hu M, Li Y, Liu Y, Hong L. Punicalagin suppresses the proliferation and invasion of cervical cancer cells through inhibition of the β-catenin pathway. Mol Med Rep. 2017 Aug;16(2):1439-1444. doi: 10.3892/mmr.2017.6687. Epub 2017 Jun 6. PMID: 28586031.


7: Pan L, Duan Y, Ma F, Lou L. Punicalagin inhibits the viability, migration, invasion, and EMT by regulating GOLPH3 in breast cancer cells. J Recept Signal Transduct Res. 2020 Apr;40(2):173-180. doi: 10.1080/10799893.2020.1719152. Epub 2020 Feb 6. PMID: 32024401.


8: Berköz M, Krośniak M. Punicalagin induces apoptosis in A549 cell line through mitochondria-mediated pathway. Gen Physiol Biophys. 2020 Nov;39(6):557-567. doi: 10.4149/gpb_2020024. PMID: 33226364.


9: Wang XZ, Zhang SF, Yang ZH, Ye ZW, Liu J. Punicalagin suppresses osteosarcoma growth and metastasis by regulating NF-κB signaling. J Biol Regul Homeost Agents. 2020 Sep-Oct;34(5):1699-1708. doi: 10.23812/20-23-A. PMID: 33148374.


10: Xie X, Hu L, Liu L, Wang J, Liu Y, Ma L, Sun G, Li C, Aisa HA, Meng S. Punicalagin promotes autophagic degradation of human papillomavirus E6 and E7 proteins in cervical cancer through the ROS-JNK-BCL2 pathway. Transl Oncol. 2022 May;19:101388. doi: 10.1016/j.tranon.2022.101388. Epub 2022 Mar 5. PMID: 35259676; PMCID: PMC8904240.


11: Silva TC, Zara ALSA, Sá FADS, Bara MTF, Ávila RI, Costa CR, Valadares MC, Santos ASD, Freitas VAQ, Silva MDRR. Antifungal potential of punicalagin against Cryptococcus neoformans species complex. Rev Inst Med Trop Sao Paulo. 2018 Oct 22;60:e60. doi: 10.1590/S1678-9946201860060. PMID: 30365643; PMCID: PMC6199124.


12: Liu W, Ou Y, Yang Y, Zhang X, Huang L, Wang X, Wu B, Huang M. Inhibitory Effect of Punicalagin on Inflammatory and Angiogenic Activation of Human Umbilical Vein Endothelial Cells. Front Pharmacol. 2021 Nov 16;12:727920. doi: 10.3389/fphar.2021.727920. PMID: 34867335; PMCID: PMC8636678.


13: Abd-Rabou AA, Shalby AB, Kotob SE. Newly Synthesized Punicalin and Punicalagin Nano-Prototypes Induce Breast Cancer Cytotoxicity Through ROS- Mediated Apoptosis. Asian Pac J Cancer Prev. 2022 Jan 1;23(1):363-376. doi: 10.31557/APJCP.2022.23.1.363. PMID: 35092406; PMCID: PMC9258674.


14: Huang T, Zhang X, Wang H. Punicalagin inhibited proliferation, invasion and angiogenesis of osteosarcoma through suppression of NF‑κB signaling. Mol Med Rep. 2020 Sep;22(3):2386-2394. doi: 10.3892/mmr.2020.11304. Epub 2020 Jul 6. PMID: 32705250; PMCID: PMC7411473.


15: Cheng X, Yao X, Xu S, Pan J, Yu H, Bao J, Guan H, Lu R, Zhang L. Punicalagin induces senescent growth arrest in human papillary thyroid carcinoma BCPAP cells via NF-κB signaling pathway. Biomed Pharmacother. 2018 Jul;103:490-498. doi: 10.1016/j.biopha.2018.04.074. Epub 2018 Apr 24. PMID: 29677534.


16: Cao Y, Ren G, Zhang Y, Qin H, An X, Long Y, Chen J, Yang L. A new way for punicalagin to alleviate insulin resistance: regulating gut microbiota and autophagy. Food Nutr Res. 2021 Jul 1;65. doi: 10.29219/fnr.v65.5689. PMID: 34262422; PMCID: PMC8254469.


17: Chen XX, Khyeam S, Zhang ZJ, Zhang KY. Granatin B and punicalagin from Chinese herbal medicine pomegranate peels elicit reactive oxygen species- mediated apoptosis and cell cycle arrest in colorectal cancer cells. Phytomedicine. 2022 Mar;97:153923. doi: 10.1016/j.phymed.2022.153923. Epub 2022 Jan 4. PMID: 35026619.


18: Adams LS, Seeram NP, Aggarwal BB, Takada Y, Sand D, Heber D. Pomegranate juice, total pomegranate ellagitannins, and punicalagin suppress inflammatory cell signaling in colon cancer cells. J Agric Food Chem. 2006 Feb 8;54(3):980-5. doi: 10.1021/jf052005r. PMID: 16448212.


19: Benchagra L, Berrougui H, Islam MO, Ramchoun M, Boulbaroud S, Hajjaji A, Fulop T, Ferretti G, Khalil A. Antioxidant Effect of Moroccan Pomegranate (Punica granatum L. Sefri Variety) Extracts Rich in Punicalagin against the Oxidative Stress Process. Foods. 2021 Sep 18;10(9):2219. doi: 10.3390/foods10092219. PMID: 34574329; PMCID: PMC8469689.


20: Tang JM, Min J, Li BS, Hong SS, Liu C, Hu M, Li Y, Yang J, Hong L. Therapeutic Effects of Punicalagin Against Ovarian Carcinoma Cells in Association With β-Catenin Signaling Inhibition. Int J Gynecol Cancer. 2016 Nov;26(9):1557-1563. doi: 10.1097/IGC.0000000000000805. PMID: 27540692.